US5821324A - Ultraviolet curable epoxidized alkyds - Google Patents
Ultraviolet curable epoxidized alkyds Download PDFInfo
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- US5821324A US5821324A US08/762,251 US76225196A US5821324A US 5821324 A US5821324 A US 5821324A US 76225196 A US76225196 A US 76225196A US 5821324 A US5821324 A US 5821324A
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- United States
- Prior art keywords
- alkyd
- fatty acid
- resin
- accordance
- anhydride
- Prior art date
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/027—Polycondensates containing more than one epoxy group per molecule obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/46—Polyesters chemically modified by esterification
- C08G63/48—Polyesters chemically modified by esterification by unsaturated higher fatty oils or their acids; by resin acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
- C08G63/553—Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/91—Polymers modified by chemical after-treatment
- C08G63/914—Polymers modified by chemical after-treatment derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/918—Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/109—Polyester
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/111—Polymer of unsaturated acid or ester
Definitions
- This invention relates to solventless, internally plasticized epoxy compositions which cure rapidly in ultraviolet light.
- a suitable photoinitiator such as triphenylsulfonium hexafluorophosphate ( ⁇ )- 3 S + PF 6 - !, is required.
- Sunlight or UV lamps may be used as radiation sources.
- the mechanism of cure is cationic rather than free radical.
- a strong acid HPF 6
- This acid initiates crosslinking through oxirane rings resulting in a network polymer.
- Alkyds are oil modified polyesters. Without oil modification, the polyester is a brittle solid. By incorporating unsaturated fatty acids into the polyester, a film with the desired flexibility can be obtained.
- Alkyds are comprised of an anhydride or diacid, a polyol, and unsaturated fatty acids. Examples of these would be phthalic anhydride, glycerine, and tall oil fatty acid. Vegetable oils, such as soybean oil, contribute both polyol and unsaturated fatty acids to an alkyd formulation. The cure of an alkyd is through autoxidation by a free radical mechanism. The sites of crosslinking are carbons adjacent to unsaturation. Alkyds are one of the most widely used protective coatings due to their durability and relatively low cost. Alkyds typically contain solvents for viscosity reduction.
- epoxy resins are multifunctional glycidyl ethers derived from the reaction of bisphenol A and epichlorhydrin.
- the oxirane rings of these resins react with amine curing agents, such as reactive polyamides, by chemical addition.
- the resulting polymer is widely used in protective coatings when superior corrosion and water resistance is required.
- Solvents are used to reduce the viscosity of the two component reaction mixture.
- Cycloaliphatic epoxy resins such as (3,4-epoxycyclohexyl)methyl-3,4-epoxycyclohexane carboxylate ##STR1## have previously been employed as solventless epoxy compositions which cure rapidly in ultraviolet light. These resins produce rigid films without the addition of a plasticizer. A flow modifier is typically added to prevent surface defects. Reactive diluents, such as propylene glycol monomethylether, may be added to reduce the viscosity of the formulation.
- Photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials were disclosed by Smith in U.S. Pat. No. 4,256,828. A process for this polymerization was disclosed by Smith in U.S. Pat. No. 4,318,766. Crivello discussed the use of a hydroxy functional flexibilizer in U.S. Pat. No. 4,175,972. These patents also involved the use of photosensitive aromatic sulfonium salts.
- epoxidized alkyd prepared from tall oil fatty acid, glycerine, and tetrahydrophthalic anhydride is illustrated as follows: ##STR3##
- a suitable photoinitiator such as triphenyl sulfonium hexafluorophosphate, is mixed with the epoxy resin at a concentration of 3% by weight. This mixture is stable in the absence of UV light. When a photon strikes the photoinitiator, a strong acid is generated which initiates rapid cationic cure through the oxirane rings of the epoxy resin.
- TOFA tall oil fatty acid
- ACINTOL® EPG tall oil fatty acid
- WFE wiped film evaporator
- Crosslinking of the oxirane rings in the TOFA or oleic acid moieties of the epoxidized alkyd in addition to cross linking of the cycloaliphatic oxirane rings of the anhydride moiety result in hard, but not brittle films.
- Glycerine is the preferred polyol of this invention.
- Trimethylolpropane can be used when a more flexible coating is desired, although a slower cure rate is obtained. Stoichiometric amounts of polyols and acids are used to form the alkyd.
- a preferred anhydride of this invention is 1,2,3,6-tetrahydrophthalic anhydride.
- the intended applications for this invention are those in which the epoxy resin viscosity can be reduced by heat or by a reactive diluent, such as limonene dioxide.
- a reactive diluent such as limonene dioxide.
- An example would be the coating of optical fibers.
- Another example would be protective coatings applied by thermal spraying.
- Equipment 500 ml, 3 neck flask equipped with an agitator, nitrogen inlet thermometer with thermowatch, steam heated precondenser, distillation head with thermometer, water cooled condenser, vacuum adapter, receiver, vacuum apparatus, heating mantle, and bubble trap.
- Equipment 500 ml, 3 neck flask equipped with an agitator, nitrogen inlet thermometer with thermowatch, steam heated precondenser, distillation head with thermometer, water cooled condenser, vacuum adapter, receiver, vacuum apparatus, heating mantle, and bubble trap.
- Equipment 500 ml, 3 neck flask equipped with an agitator, nitrogen inlet thermometer with thermowatch, steam heated precondenser, distillation head with thermometer, water cooled condenser, vacuum adapter, receiver, vacuum apparatus, heating mantle, bubble trap and a wiped film evaporator (WFE).
- WFE wiped film evaporator
- Epoxidation of the alkyds of this invention can be accomplished as follows:
- Equipment 500 ml, 3 neck flask with agitator, N 2 inlet, thermometer with thermowatch, equilibrium addition funnel, ice bath, heating mantle, bubble trap, and separatory funnels.
- LDO Limonene Dioxide
- TMP trimethylolpropane
- MTHPA methyl tetrahydrophthalic anhydride
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Epoxy Resins (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Description
TABLE I __________________________________________________________________________ Conventional Conventional Cycloaliphatic Comparison Alkyd Epoxy Epoxy Invention __________________________________________________________________________ Number of Components One Two One (plus One (plus pho- (plus drier) photoinitiator) toinitiator) Cure Type Autoxidation Chemical UV UV Cure Mechanism Free Radical Addition Cationic Cationic Cure Time Moderate to slow Moderate to slow Rapid Rapid Latent Cure Yes No Yes Yes Solvent Use Yes Yes No No Externally Plasticized No No Yes No Internally Plasticized Yes Yes No Yes (by fatty acid) (by curing agent) (by fatty acid) __________________________________________________________________________
______________________________________ Charge: 145.5 g ACINTOL ® EPG (tall oil fatty acid) 63.2 g THPA (1,2,3,6 - tetrahydrophthalic anhydride) 42.8 g Glycerine (96%) (polyol) 0.125 g Phosphoric Acid ______________________________________
______________________________________ Results: ______________________________________ Acid Number 4.3 Color, Gardner 3+ Viscosity, 25° C. 13,360 cps Iodine Value 123 Hydroxyl Value 14 Yield 92.4% ______________________________________
______________________________________ Charge: 145.5 g EMERSOL ® 221 (oleic acid) 63.2 g THPA (1,2,3,6 - tetrahydrophthalic anhydride) 42.8 g Glycerine (96%) (polyol) 0.125 g Phosphoric Acid ______________________________________
______________________________________ Results: ______________________________________ Acid Number 6.4 Color, Gardner 4 Viscosity, 25° C. 9,900 cps Iodine Value 99 Hydroxyl Value 14 Yield 90.2% ______________________________________
______________________________________ Charge: 145.5 g ACINTOL ® FA-2 (tall oil fatty acid) 63.2 g THPA (1,2,3,6 - tetrahydrophthalic anhydride) 42.8 g Glycerine (96%) (polyol) 0.125 g Phosphoric Acid ______________________________________
______________________________________ Results: ______________________________________ Before WFE Acid Number 7.1 Color, Gardner 4- Yield 94.3% ______________________________________ After WFE Residue Distillate ______________________________________ Acid Number 4.0 Acid Number 109 Color, Gardner 3 Color, Gardner 11- Viscosity, 25° C. 13,900 cps Yield 2.4% Iodine Value 123 Hydroxyl Value 19 Yield 97.6% ______________________________________
______________________________________ Charge: 75.0 g Alkyd from Examples 75.0 g Alkyd from 1&3 Example 2 150.0 g Methylene Chloride 150.0 g Methylene Chloride 96.6 g Peracetic Acid (32%) 78.2 g Peracetic Acid (32%) 2.5 g Sodium Acetate 2.0 g Sodium Acetate 23.0 g Water (distilled) 18.6 g Water (distilled) ______________________________________
______________________________________ Results: Epoxidized Epoxidized Epoxidized Alkyd Alkyd Alkyd Analysis (Example I) (Example II) (Example III) ______________________________________ Acid Number 5.0 5.4 5.2 Color, Gardner <1 <1 <1 Viscosity, 25° C. 26,000 cps 12,200 cps 34,900 cps Iodine Value 0.6 2.6 1.9 Yield 79.2 g 79.1 g 79.3 g ______________________________________
______________________________________ Cured Cured Film From Film From Epoxidized Epoxidized Cured Film From alkyd Alkyd Epoxidized Alkyd Analysis (Example I) (Example II) Example III) ______________________________________ Film Appearance Smooth, Smooth, Smooth, Glossy Glossy Glossy Cure Rate.sup.(1) ≅1 minute ≅1 minute ≅1 minute Hardness, Pencil.sup.(2) 4H 4H 4H Adhesion Cross 5 5 5 Hatch.sup.(3) Impact Resistance.sup.(4) P80F P120F P100F P20R P20R P20R Weatherability.sup.(5) Yellowing yes yes yes Film deterioration -- -- none observed Water Resistance.sup.(6) -- -- No effect Chemical Resistance.sup.(7) HCl (10%) -- -- No effect NaOH (10%) -- -- Partial film loss Acetic Acid (5%) -- -- Darkened, blisters MEK -- -- No effect CH.sub.2 Cl -- -- No effect Methanol -- -- No effect Ethyl Acetate -- -- No effect Xylene -- -- No effect Xylene/IPA (50/50) -- -- No effect Gasoline -- -- No effect Mineral Oil -- -- No effect Ethanol (200 proof) -- -- No effect Ethanol (3A) -- -- Blisters ______________________________________ .sup.(1) Dry to touch in direct sunlight .sup.(2) 8H is hardest → HB (soft) → 6B (very soft) .sup.(3) On a scale of 1-5,5 is best .sup.(4) P = pass, F = forward, R = reverse. Highest is 160. Units are in lbs. This is a measure of flexibility. .sup.(5) After three months of outside exposure. Slight yellowing is evident within days. .sup.(6) After six months of water immersion of the panel .sup.(7) Seven day chemical spot test
______________________________________ Epoxidized Alkyd/LDO Analysis Epoxidized Alkyd (80/20) ______________________________________ Viscosity, 25° C. 31,300 cps 4,060 cps Viscosity, 40° C. 7,560 cps 1,350 cps Cured Film (Refer to Example V) Film Appearance Smooth, Glossy Smooth, Glossy Cure Rate ≅1 minute ≅1 minute Hardness, Pencil 4H 4H Adhesion, Cross Hatch 5 5 Impact Resistance P120F P80F P20R P20R ______________________________________
______________________________________ Alkyd Charge: 145.5 g ACINTOL ® EPG (tall oil fatty acid) 63.2 g THPA (1,2,3,6 - tetrahydrophthalic anhydride) 61.6 g Trimethylolpropane (TMP) (polyol) 0.125 g Phosphoric Acid ______________________________________
______________________________________ Results: TMP Based Analysis Alkyd Glycerine Based Alkyd ______________________________________ Acid Number 13.7 4.3 Color, Gardner 3+ 3+ Viscosity, 25° C. 10,500 cps 13,360 cps Iodine Value 114 123 Hydroxyl Value 23 14 Yield 89.0% 92.4% ______________________________________
______________________________________ Epoxidation Results: TMP Based Glycerine Based Epoxidized Epoxidized Alkyd Analysis Alkyd (Example I) ______________________________________ Acid Number 10.1 5.0 Color, Gardner <1 <1 Viscosity, 25° C. 22,850 cps 26,000 cps Iodine Value 3.1 0.6 Yield 81.3 g 79.2 g ______________________________________
______________________________________ Results: TMP Based Glycerine Based Analysis Cured Material Cured Material ______________________________________ Film Appearance Smooth, Glossy Smooth, Glossy Cure Rate ≅2.5 minutes ≅1 minute Hardness, Pencil 2H 4H Adhesion, Cross Hatch 5 5 Impact Resistance P160F P80F P40R P20R ______________________________________
______________________________________ Alkyd Charge: 145.5 g ACINTOL ® EPG (tall oil fatty acid) 63.2 g MTHPA 40.7 g Glycerine (96%) (polyol) 0.125 g Phosphoric Acid ______________________________________
______________________________________ Results: Analysis MTHPA Based Alkyd THPA Based Alkyd ______________________________________ Acid Number 11.9 4.0 Color, Gardner 2+ 3 Viscosity, 25° C. 9,300 cps 13,900 cps Iodine Value 120 123 Hydroxyl Value 25 19 Yield 90.5% 92.0% ______________________________________
______________________________________ Epoxidation Results: MTHPA Based THPA Based Epoxidized Epoxidized Alkyd Analysis Alkyd (Example III) ______________________________________ Acid Number 6.3 5.2 Color, Gardner <1 <1 Viscosity, 25° C. 24,500 cps 34,900 cps Iodine Value 2.2 1.9 Yield 82.9 g -- ______________________________________
______________________________________ Results: MTHPA Based THPA Based Analysis Cured Material Cured Material ______________________________________ Film Appearance Smooth, Glossy Smooth, Glossy Cure Rate ≅1.5 minutes ≅1 minute Hardness, Pencil 4H 4H Adhesion, Cross Hatch 3 5 Impact Resistance P140F P100F F20R P20R ______________________________________
Claims (8)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US08/762,251 US5821324A (en) | 1995-02-15 | 1996-12-09 | Ultraviolet curable epoxidized alkyds |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/388,926 US5612445A (en) | 1995-02-15 | 1995-02-15 | Ultraviolet curable epoxidized alkyds |
US08/762,251 US5821324A (en) | 1995-02-15 | 1996-12-09 | Ultraviolet curable epoxidized alkyds |
Related Parent Applications (1)
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US08/388,926 Division US5612445A (en) | 1995-02-15 | 1995-02-15 | Ultraviolet curable epoxidized alkyds |
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US5821324A true US5821324A (en) | 1998-10-13 |
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US08/388,926 Expired - Lifetime US5612445A (en) | 1995-02-15 | 1995-02-15 | Ultraviolet curable epoxidized alkyds |
US08/762,251 Expired - Lifetime US5821324A (en) | 1995-02-15 | 1996-12-09 | Ultraviolet curable epoxidized alkyds |
Family Applications Before (1)
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US08/388,926 Expired - Lifetime US5612445A (en) | 1995-02-15 | 1995-02-15 | Ultraviolet curable epoxidized alkyds |
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US (2) | US5612445A (en) |
EP (1) | EP0809665A4 (en) |
JP (1) | JPH11501957A (en) |
AU (1) | AU4765596A (en) |
CA (1) | CA2208853C (en) |
MX (1) | MX9706220A (en) |
WO (1) | WO1996025447A1 (en) |
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US20040013895A1 (en) * | 2002-07-17 | 2004-01-22 | Dean Roy E. | Alkyd-based free radical wood coating compositions |
US6794055B2 (en) | 2003-02-03 | 2004-09-21 | Ppg Industries Ohio, Inc. | Alkyd-based free radical cured wood stains |
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US20100217608A1 (en) * | 2001-09-03 | 2010-08-26 | Mitsubishi Denki Kabushiki Kaisha | Sound decoder and sound decoding method with demultiplexing order determination |
US20040013895A1 (en) * | 2002-07-17 | 2004-01-22 | Dean Roy E. | Alkyd-based free radical wood coating compositions |
US20060035099A1 (en) * | 2002-07-17 | 2006-02-16 | Dean Roy E | Alkyd-based free radical wood coating compositions |
US7001667B2 (en) | 2002-07-17 | 2006-02-21 | Ppg Industries Ohio, Inc. | Alkyd-based free radical wood coating compositions |
US7387843B2 (en) | 2002-07-17 | 2008-06-17 | Ppg Industries Ohio, Inc. | Alkyd-based free radical wood coating compositions |
US6794055B2 (en) | 2003-02-03 | 2004-09-21 | Ppg Industries Ohio, Inc. | Alkyd-based free radical cured wood stains |
US20120082182A1 (en) * | 2009-06-08 | 2012-04-05 | Sms Siemag Aktiengesellschaft | Integration of an optical waveguide of a sensor into a component |
Also Published As
Publication number | Publication date |
---|---|
US5612445A (en) | 1997-03-18 |
WO1996025447A1 (en) | 1996-08-22 |
AU4765596A (en) | 1996-09-04 |
MX9706220A (en) | 1997-12-31 |
EP0809665A4 (en) | 1998-05-20 |
JPH11501957A (en) | 1999-02-16 |
CA2208853A1 (en) | 1996-08-22 |
CA2208853C (en) | 2002-04-30 |
EP0809665A1 (en) | 1997-12-03 |
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